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A novel chaetoglobosin named penochalasin I ( 1 ) with a unprecedented six-cyclic 6/5/6/5/6/13 fused ring system, and another new chaetoglobosin named penochalasin J ( 2 ), along with chaetoglobosins G, F, C, A, E, armochaetoglobosin I, and cytoglobosin C ( 3 - 9 ) were isolated from the culture of Penicillium chrysogenum V11. Their structures were elucidated by 1D, 2D NMR spectroscopic analysis and high resolution mass spectroscopic data. The absolute configuration of compounds 1 and 2 were determined by comparing the theoretical electronic circular dichroism (ECD) calculation with the experimental CD. Compound 1 was the first example, with a six-cyclic fused ring system formed by the connection of C-5 and C-2' of the chaetoglobosin class. Compounds 5 - 8 remarkably inhibited the plant pathogenic fungus R. solani (minimum inhibitory concentrations (MICs) = 11.79-23.66 μM), and compounds 2 , 6 , and 7 greatly inhibited C. gloeosporioides (MICs = 23.58-47.35 μM), showing an antifungal activity higher than that of carbendazim. Compound 1 exhibited marked cytotoxicity against MDA-MB-435 and SGC-7901 cells (IC 50 &lt; 10 μM), and compounds 6 and 9 showed potent cytotoxicity against SGC-7901 and A549 cells (IC 50 &lt; 10 μM).

Bioactive Chaetoglobosins from the Mangrove Endophytic Fungus Penicillium chrysogenum